2-Ethylaminoethyldimethylamine → 6-Chloro-N-[2-(dimethylamino)ethyl]-N-ethylpyridine-3-sulfonamide

HRID 748520Notes

Reaction equation

HRID 748520 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][N:6]([CH3:8])[CH3:7])[CH3:2].[Cl:9][C:10]1[N:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(Cl)Cl>[Cl:9][C:10]1[N:15]=[CH:14][C:13]([S:16]([N:3]([CH2:4][CH2:5][N:6]([CH3:8])[CH3:7])[CH2:1][CH3:2])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 671622-EthylaminoethyldimethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 858730786-Chloro-N-[2-(dimethylamino)ethyl]-N-ethylpyridine-3-sulfonamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N′-ethyl-N,N-dimethylethane-1,2-diamine (0.62 mL, 4.4 mmol) in methylene chloride (10 mL) was added 6-chloropyridine-3-sulfonylchloride (0.85 g, 4 mmol; described in: Naegeli, C. et al. Helv. Chim. Actal. 1938, 21, 1746-1750) dissolved in methylene chloride (10 mL) dropwise. The reaction mixture was stirred for 30 min at room temperature followed by the extraction with aqueous HCl (5%). The acidic water layer was alkalized with an aqueous saturated solution of NaHCO3 and extracted with methylene chloride. The organic phase was dried (Na2SO4) and evaporated in vacuo to give 0.7 gram (60% yield) of the title compound: MS (ES) m/z 292 (M++1).

Workup

  1. extractionfollowed by the extraction with aqueous HCl (5%)
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0ae60bf2444428eab492819cf7c222d
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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